Milford's Rail Trail is the opposite of what I wanted. I'm smitten.
Aug 18, 2026
t was one of those bored-parent Saturdays that are hard to explain to people who don’t have young children. A weekend with no plans and no obligations is a thing I normally cherish like a rare diamond, and now that I was sitting inside one, I couldn’t put my finger on what was missing.
It was a gorgeous day. Not a cloud in the sky, the high topping out around 84 degrees with just a pinch of humidity. New England issues roughly six and a half of these per calendar year, and most of them, by my accounting, have the decency to land on a Wednesday. So the scorecard said this should have been a Saturday we were all thrilled to be alive for.
At around 2 p.m., the hankering started.
Pizza.
Pizza is usually our Friday night thing, but the night before we’d decided to forgo it in favor of scrounging around the refrigerator for leftovers and assembling a meal that ultimately became chicken fingers our daughter didn’t much eat. So the craving carried over, and it got specific in the night, the way cravings do. It wasn’t just pizza. It was a very particular, mostly unattainable kind of pie, and not just the pie but the room you eat it in: a dine-in pizzeria that, to the best of my knowledge, doesn’t exist anywhere in the greater 495 corridor.
Kelly suggested Town Spa, the bar pizza place in Stoughton, which is fabulous and among my favorites of the genre. Town Spa is also cash only, and in 2026 cash only is a chore. Not only do I have to drive 30-plus minutes from Franklin to Stoughton, I first have to interact with either a banker or an ATM that’ll charge me some ridiculous fee for the privilege of accessing my own money. Pass.
No, the place I actually wanted, the place I’d have been standing inside in a heartbeat if geography weren’t a thing, was a place called Barnaby’s in Northbrook, Illinois, just outside Chicago.
Chicago, as I’ve written and said out loud more times than my wife would prefer, is the best food city and greater metropolitan area on the planet, and a top pizza city besides. Barnaby’s does tavern style: the cracker-thin crust, cut in squares. I wanted tavern style, cut in squares. What’s more, Barnaby’s, or at least my childhood memory of Barnaby’s, does pitchers of beer. I want to be clear that I didn’t drink pitchers of beer at Barnaby’s as a child.
Pitchers of beer, in 2026, are an alien concept. They’re either illegal, or restaurants figured out the economics are unfavorable, or, most likely, beer became a premium menu beverage and consumers now prefer their brews poured into some sort of specialty glass. I’m nostalgic for pitchers of cheap light beer of yesteryear. I’m also the exact modern-day beer snob who asks for a sample and then swirls and sniffs it like a sommelier in an ascot. I digress.
If there’s a place near the MetroWest/495 corridor doing spectacular dine-in pizza with cheap beer, or better yet pitchers of cheap beer, please let me know. I’m serious. The comments are open.
So I was sitting in a lawn chair in my driveway on a spectacularly beautiful afternoon, keeping half an eye on my 4-year-old, who was eating raw honey off a spoon for reasons she declined to share, when it hit me. There was an option. Not the ideal pizza experience I was specifically envisioning in that moment, but one that would satisfy roughly 78% of it.
Twenty minutes later we were parked on Main Street in Milford.
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